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Our top choices for Winchester hotels

Wingate by Wyndham North East

Wingate by Wyndham North East
3.0 star property
North East
8.2 out of 10, Very good, (1,000 reviews)
"Great staff, clean rooms, and great breakfast options!"
United States
Aidan
The price is CA $122
CA $137 total
includes taxes & fees
Jul 26 - Jul 27
Wingate by Wyndham North East

Residence Inn By Marriott Wilmington

Residence Inn By Marriott Wilmington
3.0 star property
Wilmington
The price is CA $208
CA $231 total
includes taxes & fees
Jul 22 - Jul 23
Residence Inn By Marriott Wilmington

Fairfield Inn by Marriott Kennett Square Brandywine Valley

Fairfield Inn by Marriott Kennett Square Brandywine Valley
3.0 star property
Kennett Square
8.8 out of 10, Excellent, (1,001 reviews)
"Great location, awesome breakfast and super helpful and friendly staff. Tyrone was especially kind and helpful."
United States
Juliette
The price is CA $142
CA $157 total
includes taxes & fees
Jul 23 - Jul 24
Fairfield Inn by Marriott Kennett Square Brandywine Valley

Red Roof Inn Perryville

Red Roof Inn Perryville
2.0 star property
Perryville
9.0 out of 10, Wonderful, (207 reviews)
"Clean and peaceful place."
United States
Eddy
The price is CA $112
CA $126 total
includes taxes & fees
Jul 20 - Jul 21
Red Roof Inn Perryville

Ramada by Wyndham Newark/Wilmington

Ramada by Wyndham Newark/Wilmington
3.0 star property
Newark
7.2 out of 10, Good, (1,012 reviews)
"It was clean, breakfast was good, and good value. "
United States
George
The price is CA $99
CA $109 total
includes taxes & fees
Jul 20 - Jul 21
Ramada by Wyndham Newark/Wilmington

Holiday Inn Express North East by IHG

Holiday Inn Express North East by IHG
2.5 star property
North East
8.4 out of 10, Very good, (584 reviews)
"Night audit clerk was wonderful! Great customer service! Property was clean, accommodations were comfortable. Breakfast has a nice selection."
United States
Andrea
The price is CA $150
CA $168 total
includes taxes & fees
Aug 2 - Aug 3
Holiday Inn Express North East by IHG

Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
2.0 star property
Havre De Grace
6.6 out of 10, (1,003 reviews)
"The room was very decent and clean. The staff was very helpful. There was little housekeeper service during my 4 day stay"
United States
Anthony
The price is CA $77
CA $86 total
includes taxes & fees
Jul 20 - Jul 21
Super 8 by Wyndham Havre De Grace Aberdeen Area

Courtyard by Marriott Newark-University of Delaware

Courtyard by Marriott Newark-University of Delaware
3.0 star property
Newark
9.0 out of 10, Wonderful, (592 reviews)
"Clean and close to campus"
United States
Adam
The price is CA $133
CA $148 total
includes taxes & fees
Jul 19 - Jul 20
Courtyard by Marriott Newark-University of Delaware

Artelo

Artelo
2.0 star property
Kennett Square
9.8 out of 10, Exceptional, (147 reviews)
"Love the art work and the location!! Very clean and comfortable room 👌"
United States
Jacqueline
The price is CA $195
CA $217 total
includes taxes & fees
Jul 20 - Jul 21
Artelo

Comfort Inn & Suites North East

Comfort Inn & Suites North East
2.5 star property
North East
8.0 out of 10, Very good, (711 reviews)
"Great value for the area exactly what I needed it to be"
United States
Kristin
The price is CA $129
CA $145 total
includes taxes & fees
Aug 6 - Aug 7
Comfort Inn & Suites North East

Inn at Mendenhall

Inn at Mendenhall
4.0 star property
Chadds Ford
9.0 out of 10, Wonderful, (1,013 reviews)
"This is our second time to visit Brandywine area and the hotel is perfect for getting to and from the properties. Staff is so nice and helpful. Rooms are pleasant and comfortable. Great breakfast!"
United States
Judith
The price is CA $188
CA $209 total
includes taxes & fees
Jul 29 - Jul 30
Inn at Mendenhall

Hilton Garden Inn Kennett Square

Hilton Garden Inn Kennett Square
3.0 star property
Kennett Square
8.4 out of 10, Very good, (995 reviews)
"The property was very nice and well kept close proximity to restaurants and stores."
United States
Cynthia
The price is CA $172
CA $190 total
includes taxes & fees
Aug 16 - Aug 17
Hilton Garden Inn Kennett Square

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (409 reviews)
"Great place to stay"
United States
Angelique
The price is CA $167
CA $185 total
includes taxes & fees
Jul 19 - Jul 20
Fairfield Inn & Suites by Marriott Middletown

Courtyard By Marriott New Castle

Courtyard By Marriott New Castle
3.0 star property
New Castle
8.8 out of 10, Excellent, (301 reviews)
"It was decent"
United States
Diana
The price is CA $173
CA $192 total
includes taxes & fees
Jul 27 - Jul 28
Courtyard By Marriott New Castle

Great Wolf Lodge Perryville

Great Wolf Lodge Perryville
2.0 star property
Perryville
8.8 out of 10, Excellent, (261 reviews)
"Good location enjoyed the trip with family"
United States
Franceen
The price is CA $251
CA $281 total
includes taxes & fees
Jul 22 - Jul 23
Great Wolf Lodge Perryville

Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG
2.5 star property
Middletown
9.2 out of 10, Wonderful, (703 reviews)
"Very clean enjoyed my stay"
United States
Yahira
The price is CA $124
CA $138 total
includes taxes & fees
Aug 16 - Aug 17
Holiday Inn Express & Suites Middletown by IHG

Best Western Plus Newark/Christiana Inn

Best Western Plus Newark/Christiana Inn
2.5 star property
Bear
8.2 out of 10, Very good, (366 reviews)
"Great place to stay"
United States
Nysier
The price is CA $118
CA $131 total
includes taxes & fees
Aug 5 - Aug 6
Best Western Plus Newark/Christiana Inn

Hampton Inn Elkton

Hampton Inn Elkton
2.5 star property
Elkton
8.6 out of 10, Excellent, (857 reviews)
"Great place to stay"
United States
Jeffery
The price is CA $143
CA $160 total
includes taxes & fees
Aug 12 - Aug 13
Hampton Inn Elkton

Elkton Lodge - Newark - Elkton - University Gateway

Elkton Lodge - Newark - Elkton - University Gateway
2.0 star property
Elkton
8.8 out of 10, Excellent, (46 reviews)
"Room was exactly as advertised. Right economic choice for our 1 night stay."
United States
John
The price is CA $110
CA $148 total
includes taxes & fees
Aug 2 - Aug 3
Elkton Lodge - Newark - Elkton - University Gateway

Comfort Inn & Suites Newark - Wilmington

Comfort Inn & Suites Newark - Wilmington
2.5 star property
Newark
9.0 out of 10, Wonderful, (1,143 reviews)
"My stay was very comfortable! I stay at this location every time I'm in Newark."
United States
Renee
The price is CA $130
CA $144 total
includes taxes & fees
Aug 6 - Aug 7
Comfort Inn & Suites Newark - Wilmington
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winchester Hotel Reviews

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Frequently asked questions

What is the best area to stay in Winchester?
The best area to stay in Winchester is the historic Old Town, which is the heart of the city and offers a distinctive experience.

Old Town is a very walkable district centred around the Loudoun Street Pedestrian Mall, a brick-paved street closed to vehicle traffic. Here, you'll find a wide selection of independent shops, local restaurants, and historic buildings, including the Handley Regional Library and the Old Court House Civil War Museum. The area retains much of its 18th and 19th-century architecture, providing a pleasant backdrop for a stroll.

Couples often find Old Town ideal for a romantic getaway. The evening atmosphere is particularly pleasant, with many restaurants offering outdoor seating and the pedestrian mall providing a charming setting for an evening walk. You're also close to several historic sites, such as George Washington's Office Museum.

Solo travellers looking for convenience and a sense of place will also appreciate Old Town. Everything you need is within easy reach, from coffee shops for a morning pick-me-up to cultural attractions, all accessible on foot.
When is the best time to go to Winchester?
The best areas to stay in Winchester are the historic downtown district and the area around Apple Blossom Mall for convenience.

The historic downtown is ideal for those who appreciate history and being able to walk to attractions. This area is centred around the Old Town Walking Mall, a pedestrian-only zone lined with boutiques, restaurants, and historic buildings. You'll find landmarks like the Handley Regional Library and the Winchester-Frederick County Historical Society nearby. The streets are generally well-maintained and offer a pleasant strolling experience.

Couples often enjoy the downtown area for its romantic charm and access to fine dining and cultural experiences. They can easily spend an evening exploring the shops, enjoying a meal at one of the many independent restaurants, or catching a show at a local theatre.

For families or those looking for modern conveniences and easy access to shopping, the area around Apple Blossom Mall to the west of downtown is a practical choice. Here, you'll find a range of contemporary hotels with amenities like indoor pools and complimentary breakfast. This location provides straightforward access to major roads, making day trips to nearby attractions simple.

Families will appreciate the convenience of having shopping and casual dining options within a short drive.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Winchester.
How can I save on a Winchester hotel booking with Expedia?
Members always get our best prices. Find our best Winchester hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Winchester hotel?
Prices for hotels in Winchester often vary, but you can find a great deal from CA $86 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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